Record Information
Version1.0
Creation date2011-09-21 00:15:29 UTC
Update date2015-07-21 06:57:15 UTC
Primary IDFDB022533
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiadenosine hexaphosphate
DescriptionDiadenosine hexaphosphate (AP6A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are AP3A, AP4A, AP5A, and AP6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP6A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP6A have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. AP6A have been identified in human platelets and shown to be an important modulator of cardiovascular function. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 16401072, 12738682, 10094777) [HMDB]
CAS Number56983-23-4
Structure
Thumb
Synonyms
SynonymSource
Adenosine 5'-hexaphosphate 5'-ester with adenosineChEBI
Adenosine-(5')-hexaphospho-(5')-adenosineChEBI
Ap(6)aChEBI
AP6aChEBI
AppppppAChEBI
Diadenosine 5',5''''-P1,P6-hexaphosphateChEBI
P1,P6-Di(adenosine-5')hexaphosphateChEBI
Adenosine 5'-hexaphosphoric acid 5'-ester with adenosineGenerator
Diadenosine 5',5''''-P1,P6-hexaphosphoric acidGenerator
P1,P6-Di(adenosine-5')hexaphosphoric acidGenerator
Diadenosine hexaphosphoric acidGenerator
Adenosine 5'-(heptahydrogen hexaphosphate) p->5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaphosphate)5'-5'-ester with adenosineHMDB
P1,P6-Bis(5'-adenosyl)hexaphosphoric acidHMDB
p(1),p(6)-Bis(5'-adenosyl)hexaphosphoric acidHMDB
Diadenosine hexaphosphateChEBI
Adenosine 5'-(heptahydrogen hexaate) P->5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaate)5'-5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaphosphate) P->5'-ester with adenosinehmdb
Adenosine 5'-hexaate 5'-ester with adenosineChEBI
Adenosine 5'-hexaic acid 5'-ester with adenosineGenerator
Adenosine-(5')-hexaO-(5')-adenosineChEBI
Ap(6)Ahmdb
AP6Ahmdb
Diadenosine 5',5''''-P1,P6-hexaateChEBI
Diadenosine 5',5''''-P1,P6-hexaic acidGenerator
Diadenosine hexaateChEBI
Diadenosine hexaic acidGenerator
P1,P6-Di(adenosine-5')hexaateChEBI
P1,P6-Di(adenosine-5')hexaic acidGenerator
P1,P6-di(Adenosine-5')hexaphosphatehmdb
Predicted Properties
PropertyValueSource
Water Solubility6.99 g/LALOGPS
logP0.26ALOGPS
logP-10ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.28ChemAxon
pKa (Strongest Basic)5.3ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area527.03 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity187.85 m³·mol⁻¹ChemAxon
Polarizability76.38 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30N10O25P6
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid
InChI IdentifierInChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
InChI KeyPZCFFCOJNXGTIM-XPWFQUROSA-N
Isomeric SMILESNC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1
Average Molecular Weight996.3468
Monoisotopic Molecular Weight995.980925632
Classification
Description Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Purine ribonucleoside polyphosphate
  • Purine nucleotide sugar
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Phosphoric acid ester
  • Imidolactam
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910110002-59d115c90a4481a6b007Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d3bcef479d59e691d5b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-8dec47b8f02e8a6ac5a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0700000209-de23da8b809775f36d57Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000200-eec87d1063e1b19d703aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-1902401000-c06f9d4097503496c4b3Spectrum
NMRNot Available
ChemSpider ID110267
ChEMBL IDNot Available
KEGG Compound IDC20190
Pubchem Compound ID123694
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01282
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDB6P
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference